Acetic Acid → HCID 59543456, compound

HRID 1798943Notes

Reaction equation

HRID 1798943 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:14][C:15](=O)[CH3:16].Cl.[C:19](O)(=O)C>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH:15]3[CH2:16][CH2:19][CH2:14]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 313Hydrochloric AcidHCID 57980628HCID 57980628, compound

Product 1

HCID 59543456HCID 59543456, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-1′,2′,3′,4′,5′,6′-hexahydro-[2,4′]bipyridinyl (6.4 g, 18.02 mmol) was dissolved in 2% acetic acid in MeOH (40 ml). Propanone (8 mL, 113 mmol) and Na(CN)BH3 (3.6 g, 57 mmol) were added. The reaction mixture was stirred at RT overnight. The reaction mixture was added 1N HCl, filtered and concentrated in vacuo. The compound was dissolved in water and the pH was adjusted to 12, then extracted with DCM (3×200 mL). The crude product was treated with 1N HCl for 1 hour and extracted with diethyl ether to remove impurities. The aqueous phase was pH adjusted to pH=5.8-9. Extraction with ethyl acetate (3×100 mL) The organic phase was dried with Na2CO3, filtered and evaporation gave 4.6 g (86%) white crystals.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe compound was dissolved in water
  4. extractionextracted with DCM (3×200 mL)
  5. additionThe crude product was treated with 1N HCl for 1 hour
  6. extractionextracted with diethyl ether
  7. customto remove impurities
  8. extractionExtraction with ethyl acetate (3×100 mL) The organic phase
  9. dry with materialwas dried with Na2CO3
  10. filtrationfiltered
  11. customevaporation

Sources & evidence

ORD record
ord-ed684f2a5b074ea69c6ae9a40341581a
Source dataset
uspto-grants-2013_01
Patent number
US08344001B2

Reaction notes

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